Base-promoted formal arylation of benzo[d]oxazoles with acyl chloride

J Org Chem. 2013 Dec 6;78(23):12076-81. doi: 10.1021/jo402106q. Epub 2013 Nov 18.

Abstract

A base-promoted formal arylation of benzo[d]oxazoles with acyl chloride was achieved in moderate to good yields. This reaction was triggered by the N-acylation of oxazole to form an iminium intermediate. Then, the addition of H2O to the iminium formed the hemiacetal intermediate. After the sequential ring-opening, extrusion of CO, the ring closure, the dehydration delivered the formal arylation product. In comparison with the transition-metal-catalyzed methodology, it represents an alternative arylation method leading to 2-arylbenzooxazole.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzoxazoles / chemical synthesis*
  • Benzoxazoles / chemistry*
  • Hydrocarbons, Chlorinated / chemistry*
  • Molecular Structure

Substances

  • Benzoxazoles
  • Hydrocarbons, Chlorinated